ES2641478T3 - Derivados de 3-acetilamino-1-(fenil-heteroaril-aminocarbonil o fenil-heteroaril-carbonilamino)benceno para el tratamiento de trastornos hiperproliferativos - Google Patents
Derivados de 3-acetilamino-1-(fenil-heteroaril-aminocarbonil o fenil-heteroaril-carbonilamino)benceno para el tratamiento de trastornos hiperproliferativos Download PDFInfo
- Publication number
- ES2641478T3 ES2641478T3 ES14712631.2T ES14712631T ES2641478T3 ES 2641478 T3 ES2641478 T3 ES 2641478T3 ES 14712631 T ES14712631 T ES 14712631T ES 2641478 T3 ES2641478 T3 ES 2641478T3
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- Spain
- Prior art keywords
- amino
- benzamide
- trifluoromethoxy
- phenyl
- morpholin
- Prior art date
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- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 96
- 238000011282 treatment Methods 0.000 title claims description 17
- 230000003463 hyperproliferative effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 487
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 279
- 239000000203 mixture Substances 0.000 claims abstract description 248
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 173
- 125000001424 substituent group Chemical group 0.000 claims abstract description 125
- 125000005843 halogen group Chemical group 0.000 claims abstract description 121
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 111
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 103
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 92
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 83
- 125000003118 aryl group Chemical group 0.000 claims abstract description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 58
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 53
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 51
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 45
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 44
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims abstract description 40
- 239000012453 solvate Substances 0.000 claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 35
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 34
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims abstract description 32
- 125000004429 atom Chemical group 0.000 claims abstract description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 27
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 26
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 21
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 21
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 16
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims abstract description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 12
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 146
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 89
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 88
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 44
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
- 102000013814 Wnt Human genes 0.000 claims description 36
- 108050003627 Wnt Proteins 0.000 claims description 36
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 28
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 28
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 238000005859 coupling reaction Methods 0.000 claims description 23
- 229910052763 palladium Inorganic materials 0.000 claims description 23
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 17
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- 238000010511 deprotection reaction Methods 0.000 claims description 14
- 230000011664 signaling Effects 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 9
- 230000037361 pathway Effects 0.000 claims description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 230000035772 mutation Effects 0.000 claims description 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 6
- 150000001263 acyl chlorides Chemical class 0.000 claims description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- 230000035755 proliferation Effects 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 5
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 229940095102 methyl benzoate Drugs 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
- 230000005856 abnormality Effects 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 230000036755 cellular response Effects 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 14
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 13
- 208000011580 syndromic disease Diseases 0.000 claims 10
- 230000024932 T cell mediated immunity Effects 0.000 claims 6
- 230000010261 cell growth Effects 0.000 claims 6
- 230000001413 cellular effect Effects 0.000 claims 6
- 230000028709 inflammatory response Effects 0.000 claims 5
- 230000004083 survival effect Effects 0.000 claims 5
- 208000003174 Brain Neoplasms Diseases 0.000 claims 4
- 208000026350 Inborn Genetic disease Diseases 0.000 claims 4
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 4
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 4
- 208000016361 genetic disease Diseases 0.000 claims 4
- MGZGHUHBXOZLPF-QGZVFWFLSA-N n-[6-(2-fluorophenyl)pyridin-3-yl]-3-[[(2r)-2-(4-methylpiperazin-1-yl)propanoyl]amino]-4-(trifluoromethoxy)benzamide Chemical compound N1([C@H](C)C(=O)NC=2C(=CC=C(C=2)C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)OC(F)(F)F)CCN(C)CC1 MGZGHUHBXOZLPF-QGZVFWFLSA-N 0.000 claims 4
- NZNXXRYDQGCBFK-UHFFFAOYSA-N 3-(2-morpholin-4-ylpropanoylamino)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C=1C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 NZNXXRYDQGCBFK-UHFFFAOYSA-N 0.000 claims 3
- TUXONIDNAJFNRA-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)propanoylamino]-4-(methylsulfonylmethyl)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C(CS(C)(=O)=O)C=1NC(=O)C(C)N1CCN(C)CC1 TUXONIDNAJFNRA-UHFFFAOYSA-N 0.000 claims 3
- QWBOSJFOAGJZPT-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)propanoylamino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C=1C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCN(C)CC1 QWBOSJFOAGJZPT-UHFFFAOYSA-N 0.000 claims 3
- XFZOXFOCQJSZKQ-UHFFFAOYSA-N 6-(2-fluorophenyl)-n-[3-(2-morpholin-4-ylpropanoylamino)-4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C=1C(NC(=O)C=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 XFZOXFOCQJSZKQ-UHFFFAOYSA-N 0.000 claims 3
- KHTVKLOEOYGTGS-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-n-[3-(2-morpholin-4-ylpropanoylamino)-4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C=1C(NC(=O)C=2C=NC(=CC=2)C=2C=C(F)C=C(F)C=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 KHTVKLOEOYGTGS-UHFFFAOYSA-N 0.000 claims 3
- QPPPKBFFQKDCMX-UHFFFAOYSA-N 6-(3-fluorophenyl)-n-[3-(2-morpholin-4-ylpropanoylamino)-4-(trifluoromethoxy)phenyl]pyridine-3-carboxamide Chemical compound C=1C(NC(=O)C=2C=NC(=CC=2)C=2C=C(F)C=CC=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 QPPPKBFFQKDCMX-UHFFFAOYSA-N 0.000 claims 3
- GYGINCUNIMDWPT-UHFFFAOYSA-N N-[6-(3,5-difluorophenyl)pyridin-3-yl]-3-(2-morpholin-4-ylpropanoylamino)-4-(trifluoromethoxy)benzamide Chemical compound FC=1C=C(C=C(C=1)F)C1=CC=C(C=N1)NC(C1=CC(=C(C=C1)OC(F)(F)F)NC(C(C)N1CCOCC1)=O)=O GYGINCUNIMDWPT-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 208000037824 growth disorder Diseases 0.000 claims 3
- 230000009401 metastasis Effects 0.000 claims 3
- FWSLMXRDOJIPST-UHFFFAOYSA-N 3-(2-morpholin-4-ylpropanoylamino)-n-(6-phenylpyridin-3-yl)-4-(trifluoromethoxy)benzamide Chemical compound C=1C(C(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 FWSLMXRDOJIPST-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 208000004998 Abdominal Pain Diseases 0.000 claims 2
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- 208000001976 Endocrine Gland Neoplasms Diseases 0.000 claims 2
- 208000028506 Familial Exudative Vitreoretinopathies Diseases 0.000 claims 2
- 208000009849 Female Genital Neoplasms Diseases 0.000 claims 2
- 201000008251 Focal dermal hypoplasia Diseases 0.000 claims 2
- 206010016970 Foot fracture Diseases 0.000 claims 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims 2
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- 208000033321 ICF syndrome Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
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- 206010059282 Metastases to central nervous system Diseases 0.000 claims 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 2
- 206010029098 Neoplasm skin Diseases 0.000 claims 2
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- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 201000010769 Prader-Willi syndrome Diseases 0.000 claims 2
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- 206010047486 Virilism Diseases 0.000 claims 2
- 208000008383 Wilms tumor Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 230000004663 cell proliferation Effects 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000011523 endocrine gland cancer Diseases 0.000 claims 2
- 201000006902 exudative vitreoretinopathy Diseases 0.000 claims 2
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
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- 230000036244 malformation Effects 0.000 claims 2
- PFSXCOASGAJFDG-UHFFFAOYSA-N n-[6-(2-fluorophenyl)pyridin-3-yl]-3-(2-morpholin-4-ylpropanoylamino)-4-(trifluoromethyl)benzamide Chemical compound C=1C(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C(C(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 PFSXCOASGAJFDG-UHFFFAOYSA-N 0.000 claims 2
- CPGGPSNHWZNRFF-UHFFFAOYSA-N n-[6-(3-fluorophenyl)pyridin-3-yl]-3-(2-morpholin-4-ylpropanoylamino)-4-(trifluoromethoxy)benzamide Chemical compound C=1C(C(=O)NC=2C=NC(=CC=2)C=2C=C(F)C=CC=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 CPGGPSNHWZNRFF-UHFFFAOYSA-N 0.000 claims 2
- XTYSNFAOAGFDBE-UHFFFAOYSA-N n-[6-(3-fluorophenyl)pyridin-3-yl]-3-[2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)propanoylamino]-4-(trifluoromethoxy)benzamide Chemical compound C1C(O2)CCC2CN1C(C)C(=O)NC(C(=CC=1)OC(F)(F)F)=CC=1C(=O)NC(C=N1)=CC=C1C1=CC=CC(F)=C1 XTYSNFAOAGFDBE-UHFFFAOYSA-N 0.000 claims 2
- YDONXTCQJOTDAZ-SFHVURJKSA-N n-[6-[4-(dimethylamino)phenyl]pyridin-3-yl]-3-[[(2s)-2-morpholin-4-ylpropanoyl]amino]-4-(trifluoromethoxy)benzamide Chemical compound N1([C@@H](C)C(=O)NC=2C(=CC=C(C=2)C(=O)NC=2C=NC(=CC=2)C=2C=CC(=CC=2)N(C)C)OC(F)(F)F)CCOCC1 YDONXTCQJOTDAZ-SFHVURJKSA-N 0.000 claims 2
- GBNHPZORLVXBCU-KRWDZBQOSA-N n-[6-[4-(hydroxymethyl)phenyl]pyridin-3-yl]-3-[[(2s)-2-morpholin-4-ylpropanoyl]amino]-4-(trifluoromethoxy)benzamide Chemical compound N1([C@@H](C)C(=O)NC=2C(=CC=C(C=2)C(=O)NC=2C=NC(=CC=2)C=2C=CC(CO)=CC=2)OC(F)(F)F)CCOCC1 GBNHPZORLVXBCU-KRWDZBQOSA-N 0.000 claims 2
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- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 1
- WMQPZCFVANWPCP-UHFFFAOYSA-N 1-n-(2-methoxyethyl)-2-[(2-morpholin-4-ylacetyl)amino]-4-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzene-1,4-dicarboxamide Chemical compound COCCNC(=O)C1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 WMQPZCFVANWPCP-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- NNRFVLAYYGPARZ-UHFFFAOYSA-N 2-[(1-morpholin-4-ylcyclopropanecarbonyl)amino]-4-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzene-1,4-dicarboxamide Chemical compound NC(=O)C1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCOCC2)CC1 NNRFVLAYYGPARZ-UHFFFAOYSA-N 0.000 claims 1
- QPWRDXFNAPYYKK-UHFFFAOYSA-N 3-(2-morpholin-4-ylpropanoylamino)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide Chemical compound C=1C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C(C(F)(F)F)C=1NC(=O)C(C)N1CCOCC1 QPWRDXFNAPYYKK-UHFFFAOYSA-N 0.000 claims 1
- BXYZWBYNNCMHGD-UHFFFAOYSA-N 3-[(1-morpholin-4-ylcyclopropanecarbonyl)amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCOCC2)CC1 BXYZWBYNNCMHGD-UHFFFAOYSA-N 0.000 claims 1
- MCDAQFFHHGMCAQ-UHFFFAOYSA-N 3-[(1-morpholin-4-ylcyclopropanecarbonyl)amino]-n-(5-phenylpyridin-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2N=CC(=CC=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCOCC2)CC1 MCDAQFFHHGMCAQ-UHFFFAOYSA-N 0.000 claims 1
- JQLQNWPQDNVZOR-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-N-(5-phenyl-1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound N1(CCOCC1)CC(=O)NC=1C=C(C(=O)NC=2OC(=NN=2)C2=CC=CC=C2)C=CC=1OC(F)(F)F JQLQNWPQDNVZOR-UHFFFAOYSA-N 0.000 claims 1
- ZXDWASAPUBVSNN-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-(2-phenyl-1,3-thiazol-5-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2SC(=NC=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 ZXDWASAPUBVSNN-UHFFFAOYSA-N 0.000 claims 1
- FKGHJQGUYZULAF-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-(3-phenyl-1,2,4-oxadiazol-5-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2ON=C(N=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 FKGHJQGUYZULAF-UHFFFAOYSA-N 0.000 claims 1
- GQWHFEOHWKHMBE-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 GQWHFEOHWKHMBE-UHFFFAOYSA-N 0.000 claims 1
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- VSGJPJQOEZVFCY-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-(5-phenyl-1,3-thiazol-2-yl)-4-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=C(C(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 VSGJPJQOEZVFCY-UHFFFAOYSA-N 0.000 claims 1
- PLVWMVVYKNZXLO-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-(6-phenylpyridin-3-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 PLVWMVVYKNZXLO-UHFFFAOYSA-N 0.000 claims 1
- XUZHPPZMZXTXTB-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-(6-phenylpyridin-3-yl)-4-(trifluoromethyl)benzamide Chemical compound FC(F)(F)C1=CC=C(C(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)C=C1NC(=O)CN1CCOCC1 XUZHPPZMZXTXTB-UHFFFAOYSA-N 0.000 claims 1
- HAXREAGPNGBQTL-UHFFFAOYSA-N 3-[(2-morpholin-4-ylacetyl)amino]-n-[5-(4-nitrophenyl)-1,3,4-thiadiazol-2-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(S1)=NN=C1NC(=O)C1=CC=C(OC(F)(F)F)C(NC(=O)CN2CCOCC2)=C1 HAXREAGPNGBQTL-UHFFFAOYSA-N 0.000 claims 1
- XUKFUAOFRUUZPD-UHFFFAOYSA-N 3-[2-(4-cyclopropylpiperazin-1-yl)propanoylamino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C=1C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N(CC1)CCN1C1CC1 XUKFUAOFRUUZPD-UHFFFAOYSA-N 0.000 claims 1
- CKDUXLHDEQCHIL-UHFFFAOYSA-N 3-[2-(4-cyclopropylpiperazin-1-yl)propanoylamino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound C=1C(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C(OC(F)(F)F)C=1NC(=O)C(C)N(CC1)CCN1C1CC1 CKDUXLHDEQCHIL-UHFFFAOYSA-N 0.000 claims 1
- RDJNTVVRRTZZNI-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)propanoylamino]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethyl)benzamide Chemical compound CN1CCN(CC1)C(C(=O)NC=1C=C(C(=O)NC=2SC(=NN2)C2=CC=CC=C2)C=CC1C(F)(F)F)C RDJNTVVRRTZZNI-UHFFFAOYSA-N 0.000 claims 1
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- PYXKGNMJTOCFNK-UHFFFAOYSA-N 3-[[1-(4-cyclopropylpiperazin-1-yl)cyclopropanecarbonyl]amino]-4-(methoxymethyl)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COCC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCN(CC2)C2CC2)CC1 PYXKGNMJTOCFNK-UHFFFAOYSA-N 0.000 claims 1
- LMXNQMCNDQEEEI-UHFFFAOYSA-N 3-[[1-(4-cyclopropylpiperazin-1-yl)cyclopropanecarbonyl]amino]-4-(methylsulfonylmethyl)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound CS(=O)(=O)CC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCN(CC2)C2CC2)CC1 LMXNQMCNDQEEEI-UHFFFAOYSA-N 0.000 claims 1
- KSVSLGRGYJVNII-UHFFFAOYSA-N 3-[[1-(4-cyclopropylpiperazin-1-yl)cyclopropanecarbonyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCN(CC2)C2CC2)CC1 KSVSLGRGYJVNII-UHFFFAOYSA-N 0.000 claims 1
- LZIDJDMKKTZXMT-UHFFFAOYSA-N 3-[[1-(4-cyclopropylpiperazin-1-yl)cyclopropanecarbonyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1NC(=O)C1=CC=C(OC(F)(F)F)C(NC(=O)C2(CC2)N2CCN(CC2)C2CC2)=C1 LZIDJDMKKTZXMT-UHFFFAOYSA-N 0.000 claims 1
- DZVKVGUMYHRZEX-UHFFFAOYSA-N 3-[[1-(4-methylpiperazin-1-yl)cyclopropanecarbonyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCN1C1(C(=O)NC=2C(=CC=C(C=2)C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)OC(F)(F)F)CC1 DZVKVGUMYHRZEX-UHFFFAOYSA-N 0.000 claims 1
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- ILWSOKXNXAMLLM-UHFFFAOYSA-N 3-[[1-[2-methoxyethyl(methyl)amino]cyclopropanecarbonyl]amino]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound COCCN(C1(CC1)C(=O)NC=1C=C(C(=O)NC=2SC(=NN=2)C2=CC=CC=C2)C=CC=1OC(F)(F)F)C ILWSOKXNXAMLLM-UHFFFAOYSA-N 0.000 claims 1
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- RVJQAQPBSFCKFZ-UHFFFAOYSA-N 3-[[2-(3,4-dimethylpiperazin-1-yl)acetyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)C(C)CN1CC(=O)NC1=CC(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C1OC(F)(F)F RVJQAQPBSFCKFZ-UHFFFAOYSA-N 0.000 claims 1
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- PFGQKZRTHFZWDT-UHFFFAOYSA-N 3-[[2-(4-cyclopropylpiperazin-1-yl)acetyl]amino]-4-(difluoromethoxy)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound FC(F)OC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)CN(CC1)CCN1C1CC1 PFGQKZRTHFZWDT-UHFFFAOYSA-N 0.000 claims 1
- PBESRUKRYUWGCB-UHFFFAOYSA-N 3-[[2-(4-cyclopropylpiperazin-1-yl)acetyl]amino]-4-(methoxymethyl)-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound COCC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)CN(CC1)CCN1C1CC1 PBESRUKRYUWGCB-UHFFFAOYSA-N 0.000 claims 1
- NDIHTZSIBMIILM-UHFFFAOYSA-N 3-[[2-(4-cyclopropylpiperazin-1-yl)acetyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound FC(F)(F)OC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)CN(CC1)CCN1C1CC1 NDIHTZSIBMIILM-UHFFFAOYSA-N 0.000 claims 1
- HCSYYUWBSJWLDC-UHFFFAOYSA-N 3-[[2-(4-cyclopropylpiperazin-1-yl)acetyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1NC(=O)C1=CC=C(OC(F)(F)F)C(NC(=O)CN2CCN(CC2)C2CC2)=C1 HCSYYUWBSJWLDC-UHFFFAOYSA-N 0.000 claims 1
- KPPSFOKJNKIGSC-UHFFFAOYSA-N 3-[[2-(4-cyclopropylpiperazin-1-yl)acetyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound FC1=CC=CC=C1C(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C(NC(=O)CN2CCN(CC2)C2CC2)=C1 KPPSFOKJNKIGSC-UHFFFAOYSA-N 0.000 claims 1
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- ZSRCWTPZLLQYCM-UHFFFAOYSA-N 3-[[2-(4-methyl-1,4-diazepan-1-yl)acetyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCCN1CC(=O)NC1=CC(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C1OC(F)(F)F ZSRCWTPZLLQYCM-UHFFFAOYSA-N 0.000 claims 1
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- ZHIHVAKRBQMXJL-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-4-(trifluoromethoxy)-N-[5-[2-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1CCN(CC1)CC(=O)NC=1C=C(C(=O)NC=2SC(=NN=2)C2=C(C=CC=C2)C(F)(F)F)C=CC=1OC(F)(F)F ZHIHVAKRBQMXJL-UHFFFAOYSA-N 0.000 claims 1
- XEFHDBUDMDTZFF-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-4-(trifluoromethoxy)-N-[5-[3-(trifluoromethyl)phenyl]-1,3,4-thiadiazol-2-yl]benzamide Chemical compound CN1CCN(CC1)CC(=O)NC=1C=C(C(=O)NC=2SC(=NN=2)C2=CC(=CC=C2)C(F)(F)F)C=CC=1OC(F)(F)F XEFHDBUDMDTZFF-UHFFFAOYSA-N 0.000 claims 1
- BUDSEUSTGYWPCA-UHFFFAOYSA-N 3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCN1CC(=O)NC1=CC(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C1OC(F)(F)F BUDSEUSTGYWPCA-UHFFFAOYSA-N 0.000 claims 1
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- LNUKHOVUQVDDMA-KRWDZBQOSA-N 3-[[2-[(2s)-2,4-dimethylpiperazin-1-yl]acetyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound C[C@H]1CN(C)CCN1CC(=O)NC1=CC(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C1OC(F)(F)F LNUKHOVUQVDDMA-KRWDZBQOSA-N 0.000 claims 1
- IBSFTHPGPUBNAB-QGZVFWFLSA-N 3-[[2-[(3r)-3,4-dimethylpiperazin-1-yl]acetyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)[C@H](C)CN1CC(=O)NC1=CC(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C1OC(F)(F)F IBSFTHPGPUBNAB-QGZVFWFLSA-N 0.000 claims 1
- IBSFTHPGPUBNAB-KRWDZBQOSA-N 3-[[2-[(3s)-3,4-dimethylpiperazin-1-yl]acetyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)[C@@H](C)CN1CC(=O)NC1=CC(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C1OC(F)(F)F IBSFTHPGPUBNAB-KRWDZBQOSA-N 0.000 claims 1
- VSMGPLDKOKDHHN-UHFFFAOYSA-N 3-[[2-[2-methoxyethyl(methyl)amino]acetyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1=C(OC(F)(F)F)C(NC(=O)CN(C)CCOC)=CC(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=C1 VSMGPLDKOKDHHN-UHFFFAOYSA-N 0.000 claims 1
- XNEZKBMOWBLDCT-UHFFFAOYSA-N 3-[[2-[4-(2,2-difluoroethyl)piperazin-1-yl]acetyl]amino]-n-[6-(2-fluorophenyl)pyridin-3-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1CN(CC(F)F)CCN1CC(=O)NC1=CC(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)=CC=C1OC(F)(F)F XNEZKBMOWBLDCT-UHFFFAOYSA-N 0.000 claims 1
- NTFFMNYOEUPKQU-UHFFFAOYSA-N 3-[methyl-(2-morpholin-4-ylacetyl)amino]-N-(6-phenylpyridin-3-yl)-4-(trifluoromethoxy)benzamide Chemical compound CN(C=1C=C(C(=O)NC=2C=NC(=CC=2)C2=CC=CC=C2)C=CC=1OC(F)(F)F)C(CN1CCOCC1)=O NTFFMNYOEUPKQU-UHFFFAOYSA-N 0.000 claims 1
- ZLHADKIBBRAPRP-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-3-[(2-morpholin-4-ylacetyl)amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound C=1C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C(OCC2CC2)C=1NC(=O)CN1CCOCC1 ZLHADKIBBRAPRP-UHFFFAOYSA-N 0.000 claims 1
- YNZGNMMGIWDCAW-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-3-[[2-(4-cyclopropylpiperazin-1-yl)acetyl]amino]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound C1(CC1)COC1=C(C=C(C(=O)NC=2SC(=NN=2)C2=CC=CC=C2)C=C1)NC(CN1CCN(CC1)C1CC1)=O YNZGNMMGIWDCAW-UHFFFAOYSA-N 0.000 claims 1
- XCOJBBCUQXYUCJ-UHFFFAOYSA-N 4-(cyclopropylmethoxy)-3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound C1(CC1)COC1=C(C=C(C(=O)NC=2SC(=NN=2)C2=CC=CC=C2)C=C1)NC(CN1CCN(CC1)C)=O XCOJBBCUQXYUCJ-UHFFFAOYSA-N 0.000 claims 1
- CJUIOOKKKHRBDW-UHFFFAOYSA-N 4-(difluoromethoxy)-3-[(1-morpholin-4-ylcyclopropanecarbonyl)amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound FC(F)OC1=CC=C(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)C=C1NC(=O)C1(N2CCOCC2)CC1 CJUIOOKKKHRBDW-UHFFFAOYSA-N 0.000 claims 1
- XERYACSULAQUIR-UHFFFAOYSA-N 4-(difluoromethoxy)-3-[(2-morpholin-4-ylacetyl)amino]-N-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound FC(OC1=C(C=C(C(=O)NC=2SC(=NN=2)C2=CC=CC=C2)C=C1)NC(CN1CCOCC1)=O)F XERYACSULAQUIR-UHFFFAOYSA-N 0.000 claims 1
- MHPHVFZOANJXNT-UHFFFAOYSA-N 4-(difluoromethoxy)-3-[[1-(4-methylpiperazin-1-yl)cyclopropanecarbonyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound C1CN(C)CCN1C1(C(=O)NC=2C(=CC=C(C=2)C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)OC(F)F)CC1 MHPHVFZOANJXNT-UHFFFAOYSA-N 0.000 claims 1
- RZAYXPOLDBZMMO-UHFFFAOYSA-N 4-(difluoromethoxy)-3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-n-(5-phenyl-1,3,4-thiadiazol-2-yl)benzamide Chemical compound C1CN(C)CCN1CC(=O)NC1=CC(C(=O)NC=2SC(=NN=2)C=2C=CC=CC=2)=CC=C1OC(F)F RZAYXPOLDBZMMO-UHFFFAOYSA-N 0.000 claims 1
- IAYMTGIVHBMYGA-UHFFFAOYSA-N 4-(difluoromethoxy)-n-[5-(2-methylphenyl)-1,3,4-thiadiazol-2-yl]-3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]benzamide Chemical compound C1CN(C)CCN1CC(=O)NC1=CC(C(=O)NC=2SC(=NN=2)C=2C(=CC=CC=2)C)=CC=C1OC(F)F IAYMTGIVHBMYGA-UHFFFAOYSA-N 0.000 claims 1
- LSALXJYHGMAXJO-UHFFFAOYSA-N 4-(difluoromethoxy)-n-[6-(2-fluorophenyl)pyridin-3-yl]-3-[(2-morpholin-4-ylacetyl)amino]benzamide Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)C=C1NC(=O)CN1CCOCC1 LSALXJYHGMAXJO-UHFFFAOYSA-N 0.000 claims 1
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- BCIZWNGRDUPVKI-UHFFFAOYSA-N n-[4-tert-butyl-3-[(2-morpholin-4-ylacetyl)amino]phenyl]-5-phenylthiophene-2-carboxamide Chemical compound C1=C(NC(=O)CN2CCOCC2)C(C(C)(C)C)=CC=C1NC(=O)C(S1)=CC=C1C1=CC=CC=C1 BCIZWNGRDUPVKI-UHFFFAOYSA-N 0.000 claims 1
- QYNVEPFFZUNDPY-UHFFFAOYSA-N n-[4-tert-butyl-3-[(2-morpholin-4-ylacetyl)amino]phenyl]-6-phenylpyridine-3-carboxamide Chemical compound C1=C(NC(=O)CN2CCOCC2)C(C(C)(C)C)=CC=C1NC(=O)C(C=N1)=CC=C1C1=CC=CC=C1 QYNVEPFFZUNDPY-UHFFFAOYSA-N 0.000 claims 1
- SMRXMWVWWPBBLI-UHFFFAOYSA-N n-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-3-[[2-(4-methylpiperazin-1-yl)acetyl]amino]-4-(trifluoromethoxy)benzamide Chemical compound C1CN(C)CCN1CC(=O)NC1=CC(C(=O)NC=2SC(=NN=2)C=2C(=CC=CC=2)Cl)=CC=C1OC(F)(F)F SMRXMWVWWPBBLI-UHFFFAOYSA-N 0.000 claims 1
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- UHDJRDQGPOCDFM-UHFFFAOYSA-N n-[6-(2-fluorophenyl)pyridin-3-yl]-4-methyl-3-[(1-morpholin-4-ylcyclopropanecarbonyl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=NC(=CC=2)C=2C(=CC=CC=2)F)C=C1NC(=O)C1(N2CCOCC2)CC1 UHDJRDQGPOCDFM-UHFFFAOYSA-N 0.000 claims 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/433—Thidiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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CR20160432A (es) | 2014-03-20 | 2017-07-21 | Bayer Pharma AG | Inhibidores de las vías de señalización de wnt |
CA2976971A1 (en) | 2015-02-20 | 2016-08-25 | Bayer Pharma Aktiengesellschaft | 3-carbamoylphenyl-4-carboxamide and isophtalamide derivatives as inhibitors of the wnt signalling pathway |
JP2018505906A (ja) | 2015-02-20 | 2018-03-01 | バイエル・ファルマ・アクティエンゲゼルシャフト | Wntシグナル伝達経路の阻害剤としての1,3,4−チアジアゾール−2−イル−ベンズアミド誘導体 |
US20180042931A1 (en) | 2015-02-20 | 2018-02-15 | Bayer Pharma Aktiengesellschaft | N-phenyl-(morpholin-4-yl or piperazinyl)acetamide derivatives and their use as inhibitors of the wnt signalling pathways |
-
2014
- 2014-03-17 SG SG11201507615SA patent/SG11201507615SA/en unknown
- 2014-03-17 ES ES14712631.2T patent/ES2641478T3/es active Active
- 2014-03-17 CA CA2907535A patent/CA2907535A1/en not_active Abandoned
- 2014-03-17 WO PCT/EP2014/055300 patent/WO2014147021A2/en active Application Filing
- 2014-03-17 KR KR1020157030102A patent/KR20150132556A/ko not_active Application Discontinuation
- 2014-03-17 AU AU2014234472A patent/AU2014234472A1/en not_active Abandoned
- 2014-03-17 MX MX2015013348A patent/MX2015013348A/es unknown
- 2014-03-17 EP EP14712631.2A patent/EP2976327B1/de not_active Not-in-force
- 2014-03-17 JP JP2016503626A patent/JP2016519674A/ja active Pending
- 2014-03-17 CN CN201480029301.5A patent/CN105228982B/zh not_active Expired - Fee Related
- 2014-03-17 US US14/778,568 patent/US10130633B2/en not_active Expired - Fee Related
- 2014-03-17 PE PE2015002049A patent/PE20160154A1/es not_active Application Discontinuation
- 2014-03-17 EA EA201500953A patent/EA201500953A1/ru unknown
- 2014-03-17 BR BR112015024073A patent/BR112015024073A2/pt not_active IP Right Cessation
- 2014-03-19 UY UY0001035492A patent/UY35492A/es not_active Application Discontinuation
- 2014-03-20 TW TW103110560A patent/TW201444793A/zh unknown
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2015
- 2015-09-17 TN TN2015000429A patent/TN2015000429A1/en unknown
- 2015-09-18 CR CR20150500A patent/CR20150500A/es unknown
- 2015-09-18 DO DO2015000245A patent/DOP2015000245A/es unknown
- 2015-09-18 CU CUP2015000129A patent/CU20150129A7/es unknown
- 2015-09-18 PH PH12015502192A patent/PH12015502192A1/en unknown
- 2015-09-18 NI NI201500142A patent/NI201500142A/es unknown
- 2015-09-21 CL CL2015002814A patent/CL2015002814A1/es unknown
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2016
- 2016-05-24 HK HK16105879.7A patent/HK1217706A1/zh unknown
Also Published As
Publication number | Publication date |
---|---|
DOP2015000245A (es) | 2015-12-15 |
UY35492A (es) | 2014-10-31 |
NI201500142A (es) | 2015-11-09 |
BR112015024073A2 (pt) | 2018-05-08 |
JP2016519674A (ja) | 2016-07-07 |
AU2014234472A1 (en) | 2015-10-29 |
WO2014147021A2 (en) | 2014-09-25 |
CL2015002814A1 (es) | 2016-04-01 |
HK1217706A1 (zh) | 2017-01-20 |
KR20150132556A (ko) | 2015-11-25 |
TW201444793A (zh) | 2014-12-01 |
SG11201507615SA (en) | 2015-10-29 |
US20160263122A1 (en) | 2016-09-15 |
EP2976327B1 (de) | 2017-06-21 |
US10130633B2 (en) | 2018-11-20 |
MX2015013348A (es) | 2016-01-20 |
WO2014147021A3 (en) | 2015-07-23 |
EP2976327A2 (de) | 2016-01-27 |
CN105228982A (zh) | 2016-01-06 |
CA2907535A1 (en) | 2014-09-25 |
EA201500953A1 (ru) | 2016-06-30 |
CU20150129A7 (es) | 2016-06-29 |
CN105228982B (zh) | 2018-03-27 |
CR20150500A (es) | 2016-01-29 |
PE20160154A1 (es) | 2016-04-20 |
TN2015000429A1 (en) | 2017-01-03 |
PH12015502192A1 (en) | 2016-01-25 |
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